diff --git a/codex-rs/tui/src/app.rs b/codex-rs/tui/src/app.rs
index fcaf4d2290..54b6c32270 100644
--- a/codex-rs/tui/src/app.rs
+++ b/codex-rs/tui/src/app.rs
@@ -648,7 +648,9 @@ impl App {
         use tokio_stream::StreamExt;
         let (app_event_tx, mut app_event_rx) = unbounded_channel();
         let app_event_tx = AppEventSender::new(app_event_tx);
+        tui::log_windows_vt_output_mode("before_emit_project_config_warnings");
         emit_project_config_warnings(&app_event_tx, &config);
+        tui::log_windows_vt_output_mode("after_emit_project_config_warnings");
         emit_system_bwrap_warning(&app_event_tx, &config);
         tui.set_notification_settings(
             config.tui_notifications.method,
diff --git a/codex-rs/tui/src/app/startup_prompts.rs b/codex-rs/tui/src/app/startup_prompts.rs
index 802cda3f80..7749bf624f 100644
--- a/codex-rs/tui/src/app/startup_prompts.rs
+++ b/codex-rs/tui/src/app/startup_prompts.rs
@@ -60,6 +60,7 @@ pub(super) fn emit_project_config_warnings(app_event_tx: &AppEventSender, config
         message.push_str(&format!("       {reason}\n"));
     }
 
+    crate::tui::log_windows_vt_output_mode("before_project_config_warning_history");
     app_event_tx.send(AppEvent::InsertHistoryCell(Box::new(
         history_cell::new_warning_event(message),
     )));
diff --git a/codex-rs/tui/src/branch_summary.rs b/codex-rs/tui/src/branch_summary.rs
index 4698dc96e5..9ec68114cd 100644
--- a/codex-rs/tui/src/branch_summary.rs
+++ b/codex-rs/tui/src/branch_summary.rs
@@ -101,6 +101,7 @@ pub(crate) async fn current_branch_name(
     runner: &dyn WorkspaceCommandExecutor,
     cwd: &Path,
 ) -> Option<String> {
+    crate::tui::log_windows_vt_output_mode("before_status_line_branch_lookup");
     let output = run_git_command(runner, cwd, &["branch", "--show-current"])
         .await
         .ok()?;
diff --git a/codex-rs/tui/src/chatwidget/status_surfaces.rs b/codex-rs/tui/src/chatwidget/status_surfaces.rs
index e34fe4688a..9372b31a68 100644
--- a/codex-rs/tui/src/chatwidget/status_surfaces.rs
+++ b/codex-rs/tui/src/chatwidget/status_surfaces.rs
@@ -426,6 +426,7 @@ impl ChatWidget {
     /// stable project label.
     fn status_line_project_root_for_cwd(&self, cwd: &Path) -> Option<PathBuf> {
         if let Some(repo_root) = get_git_repo_root(cwd) {
+            crate::tui::log_windows_vt_output_mode("project_root_from_git");
             return Some(repo_root);
         }
 
diff --git a/codex-rs/tui/src/tui.rs b/codex-rs/tui/src/tui.rs
index 9760b598d8..4203d4935c 100644
--- a/codex-rs/tui/src/tui.rs
+++ b/codex-rs/tui/src/tui.rs
@@ -282,6 +282,26 @@ fn apply_windows_vt_output_debug_override() {
 #[cfg(not(windows))]
 fn apply_windows_vt_output_debug_override() {}
 
+#[cfg(windows)]
+fn log_windows_pending_history_lines(pending_history_lines: &[PendingHistoryLines]) {
+    if debug_windows_vt_output_mode().is_none() {
+        return;
+    }
+
+    let line_count: usize = pending_history_lines
+        .iter()
+        .map(|batch| batch.lines.len())
+        .sum();
+    tracing::info!(
+        batch_count = pending_history_lines.len(),
+        line_count,
+        "Windows pending history debug state"
+    );
+}
+
+#[cfg(not(windows))]
+fn log_windows_pending_history_lines(_pending_history_lines: &[PendingHistoryLines]) {}
+
 #[cfg(windows)]
 pub(crate) fn log_windows_vt_output_mode(phase: &'static str) {
     use windows_sys::Win32::System::Console::ENABLE_VIRTUAL_TERMINAL_PROCESSING;
@@ -868,6 +888,7 @@ impl Tui {
             return Ok(());
         }
 
+        log_windows_pending_history_lines(pending_history_lines);
         log_windows_vt_output_mode("before_insert_history");
 
         for batch in pending_history_lines.iter() {